diff --git a/httpbp/client_middlewares.go b/httpbp/client_middlewares.go
index f621a826c..3944a1fab 100644
--- a/httpbp/client_middlewares.go
+++ b/httpbp/client_middlewares.go
@@ -2,7 +2,9 @@ package httpbp
 
 import (
 	"errors"
+	"fmt"
 	"io"
+	"log/slog"
 	"net/http"
 	"strconv"
 	"sync"
@@ -200,16 +202,36 @@ func CircuitBreaker(config breakerbp.Config) ClientMiddleware {
 // Retries provides a retry middleware by ensuring certain HTTP responses are
 // wrapped in errors. Retries wraps the ClientErrorWrapper middleware, e.g. if
 // you are using Retries there is no need to also use ClientErrorWrapper.
-func Retries(limit int, retryOptions ...retry.Option) ClientMiddleware {
+func Retries(maxErrorReadAhead int, retryOptions ...retry.Option) ClientMiddleware {
 	if len(retryOptions) == 0 {
 		retryOptions = []retry.Option{retry.Attempts(1)}
 	}
 	return func(next http.RoundTripper) http.RoundTripper {
+		// include ClientErrorWrapper to ensure retry is applied for some HTTP 5xx
+		// responses
+		next = ClientErrorWrapper(maxErrorReadAhead)(next)
+
 		return roundTripperFunc(func(req *http.Request) (resp *http.Response, err error) {
+			if req.Body != nil && req.Body != http.NoBody && req.GetBody == nil {
+				slog.WarnContext(
+					req.Context(),
+					"Request comes with a Body but nil GetBody cannot be retried. httpbp.Retries middleware skipped.",
+					"req", req,
+				)
+				return next.RoundTrip(req)
+			}
+
 			err = retrybp.Do(req.Context(), func() error {
-				// include ClientErrorWrapper to ensure retry is applied for
-				// some HTTP 5xx responses
-				resp, err = ClientErrorWrapper(limit)(next).RoundTrip(req)
+				req = req.Clone(req.Context())
+				if req.GetBody != nil {
+					body, err := req.GetBody()
+					if err != nil {
+						return fmt.Errorf("httpbp.Retries: GetBody returned error: %w", err)
+					}
+					req.Body = body
+				}
+
+				resp, err = next.RoundTrip(req)
 				if err != nil {
 					return err
 				}
diff --git a/httpbp/client_middlewares_test.go b/httpbp/client_middlewares_test.go
index 426e74e35..bfd9efc59 100644
--- a/httpbp/client_middlewares_test.go
+++ b/httpbp/client_middlewares_test.go
@@ -8,6 +8,7 @@ import (
 	"io"
 	"net/http"
 	"net/http/httptest"
+	"net/url"
 	"sync"
 	"sync/atomic"
 	"testing"
@@ -256,11 +257,22 @@ func TestClientErrorWrapper(t *testing.T) {
 	})
 }
 
+func unwrapRetryErrors(err error) []error {
+	var errs interface {
+		error
+
+		Unwrap() []error
+	}
+	if errors.As(err, &errs) {
+		return errs.Unwrap()
+	}
+	return []error{err}
+}
+
 func TestRetry(t *testing.T) {
-	t.Run("retry for timeout", func(t *testing.T) {
-		const timeout = time.Millisecond * 10
+	t.Run("retry for HTTP 500", func(t *testing.T) {
 		server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			time.Sleep(timeout * 10)
+			w.WriteHeader(http.StatusInternalServerError)
 		}))
 		defer server.Close()
 
@@ -274,36 +286,72 @@ func TestRetry(t *testing.T) {
 					attempts = n + 1
 				}),
 			)(http.DefaultTransport),
-			Timeout: timeout,
 		}
-		_, err := client.Get(server.URL)
+		u, err := url.Parse(server.URL)
+		if err != nil {
+			t.Fatalf("Failed to parse url %q: %v", server.URL, err)
+		}
+		req := &http.Request{
+			Method: http.MethodPost,
+			URL:    u,
+
+			// Explicitly set Body to http.NoBody and GetBody to nil,
+			// This request should not cause Retries middleware to be skipped.
+			Body:    http.NoBody,
+			GetBody: nil,
+		}
+		_, err = client.Do(req)
 		if err == nil {
 			t.Fatalf("expected error to be non-nil")
 		}
-		expected := uint(1)
+		expected := uint(2)
 		if attempts != expected {
 			t.Errorf("expected %d, actual: %d", expected, attempts)
 		}
+		errs := unwrapRetryErrors(err)
+		if len(errs) != int(expected) {
+			t.Errorf("Expected %d retry erros, got %+v", expected, errs)
+		}
+		for i, err := range errs {
+			var ce *ClientError
+			if errors.As(err, &ce) {
+				if got, want := ce.StatusCode, http.StatusInternalServerError; got != want {
+					t.Errorf("#%d: status got %d want %d", i, got, want)
+				}
+			} else {
+				t.Errorf("#%d: %#v is not of type *httpbp.ClientError", i, err)
+			}
+		}
 	})
 
-	t.Run("retry for HTTP 500", func(t *testing.T) {
-		server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+	t.Run("retry POST+HTTPS request", func(t *testing.T) {
+		server := httptest.NewTLSServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			b, err := io.ReadAll(r.Body)
+			if err != nil {
+				t.Fatal(err)
+			}
+			expected := "{}"
+			got := string(b)
+			if got != expected {
+				t.Errorf("expected %q, got: %q", expected, got)
+			}
+			t.Logf("Full body: %q", got)
 			w.WriteHeader(http.StatusInternalServerError)
 		}))
 		defer server.Close()
 
 		var attempts uint
-		client := &http.Client{
-			Transport: Retries(
-				DefaultMaxErrorReadAhead,
-				retry.Attempts(2),
-				retry.OnRetry(func(n uint, err error) {
-					// set number of attempts to check if retries were attempted
-					attempts = n + 1
-				}),
-			)(http.DefaultTransport),
-		}
-		_, err := client.Get(server.URL)
+		t.Log(server.URL)
+		client := server.Client()
+		client.Transport = Retries(
+			DefaultMaxErrorReadAhead,
+			retry.Attempts(2),
+			retry.OnRetry(func(n uint, err error) {
+				// set number of attempts to check if retries were attempted
+				attempts = n + 1
+			}),
+		)(client.Transport)
+		_, err := client.Post(server.URL, "application/json", bytes.NewBufferString("{}"))
 		if err == nil {
 			t.Fatalf("expected error to be non-nil")
 		}
@@ -311,41 +359,44 @@ func TestRetry(t *testing.T) {
 		if attempts != expected {
 			t.Errorf("expected %d, actual: %d", expected, attempts)
 		}
+		errs := unwrapRetryErrors(err)
+		if len(errs) != int(expected) {
+			t.Errorf("Expected %d retry erros, got %+v", expected, errs)
+		}
+		for i, err := range errs {
+			var ce *ClientError
+			if errors.As(err, &ce) {
+				if got, want := ce.StatusCode, http.StatusInternalServerError; got != want {
+					t.Errorf("#%d: status got %d want %d", i, got, want)
+				}
+			} else {
+				t.Errorf("#%d: %#v is not of type *httpbp.ClientError", i, err)
+			}
+		}
 	})
 
-	t.Run("retry POST request", func(t *testing.T) {
+	t.Run("skip retry for wrongly constructed request", func(t *testing.T) {
 		server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			b, err := io.ReadAll(r.Body)
-			if err != nil {
-				t.Fatal(err)
-			}
-			expected := "{}"
-			got := string(b)
-			if got != expected {
-				t.Errorf("expected %q, got: %q", expected, got)
-			}
 			w.WriteHeader(http.StatusInternalServerError)
 		}))
 		defer server.Close()
 
-		var attempts uint
 		client := &http.Client{
 			Transport: Retries(
 				DefaultMaxErrorReadAhead,
 				retry.Attempts(2),
 				retry.OnRetry(func(n uint, err error) {
-					// set number of attempts to check if retries were attempted
-					attempts = n + 1
+					t.Errorf("Retry not skipped. OnRetry called with (%d, %v)", n, err)
 				}),
 			)(http.DefaultTransport),
 		}
-		_, err := client.Post(server.URL, "application/json", bytes.NewBufferString("{}"))
-		if err == nil {
-			t.Fatalf("expected error to be non-nil")
+		req, err := http.NewRequest(http.MethodGet, server.URL, bytes.NewBufferString("{}"))
+		if err != nil {
+			t.Fatalf("Failed to create http request: %v", err)
 		}
-		expected := uint(2)
-		if attempts != expected {
-			t.Errorf("expected %d, actual: %d", expected, attempts)
+		req.GetBody = nil
+		if _, err := client.Do(req); err == nil {
+			t.Fatalf("expected error to be non-nil")
 		}
 	})
 }